DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 09/18/2026 has been entered.
Status of the Claims
The amendment filed on 09/18/2026 has been entered. Claims 1 and 21 have been amended and claim 8 has been canceled. Thus claims 1-7, 9-16, 18 and 20-22 are currently pending; claims 12-16, 18 and 20 have been withdrawn; and claims 1-7, 9-11 and 21-22 are under examination.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1, 3-7, 9-11 and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US2003/0065233A1 (US’233) in view of Patent number CA1177095A (CA’095). The references have been cited in PTO-892 12/23/2025.
Regarding claims 1(a)-(b), 3, 5 and 21(a)-(b), US’233 teaches a production process for α-olefins and internal olefin isomers from a primary alcohol or an ether of formula (I) and a catalyst:
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Examples of the straight or branched alkyl group having 3 to 20 carbon atoms as represented by R 1 in the above formula include n-propyl, n-butyl, isobutyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, tetradecyl, hexadecyl and octadecyl. Examples of the straight or branched alkyl group having 1 to 20 carbons as represented by R2 include methyl, ethyl, n-propyl, n-butyl, isobutyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, tetradecyl, hexadecyl and octadecyl and examples of the primary alcohol include n-butanol, n-pentanol, 3-methyl-1-butanol, n-hexanol, n-octanol, n-nonanol, n-decanol, n-undecanol, n-dodecanol, n-tetradecanol and n-hexadecanol. Of these, n-hexanol, n-octanol, n-nonanol and n-decanol are preferred. Examples of the ether include methyl pentyl ether, hexyl methyl ether, methyl octy ether, methyl nonyl ether, decyl methyl ether, ethyl pentyl ether, ethyl hexyl ether, ethyl octyl ether, methyl nonyl ether, decyl methyl ether, isopropyl pentyl ether, hexyl isopropyl ether, isopropyl octyl ether, isopropyl nonyl ether, decyl isopropyl ether, dihexyl ether, dioctyl ether and didecyl ether ([0024]-[0025]).
The reaction in US’233 is preferably carried out at a temperature of 150 to 350° C. and more preferably at 200 to 320° C ([0030]). The reference further teaches that unreacted primary alcohol or ether, is separated and collected from reaction products, and at least part of the collected ether intermediate, and unreacted primary alcohol or ether is returned to the reaction system and can serve as a starting material for the reaction ([0014], [0017] and [0051]). While US’233 teaches that unreacted alcohol and ether can be returned and serve as a starting material, the reference fails to specifically teach that the dialkylether and/or 1-alcohol are combined with fresh 1-alcohol and/or fresh dialkylether, in a ratio of 30:70 to 50:50 by volume. However, since the reference teaches that the α-olefins and internal olefin isomers can be obtained from fresh primary alcohol and ether and/or from unreacted primary alcohol and ether, any combination of the fresh primary alcohol and ether and unreacted primary alcohol and ether, including the claimed ratio, would yield nothing more than the predictable α-olefins and internal olefin isomers.
Regarding claim 5, the catalyst comprises γ-alumina ([0026] and Examples 1-11).
Regarding claim 6-7 and 9, US’233 teaches that the rate at which the mixture is fed to the reactor is typically in the range of 0.1 to 50 hr −1, and preferably in the range of 0.5 to 10 hr−1 as measured in the liquid hourly space velocity (LHSV) ([0031]) and that the reaction may be carried out by using any known technique, including batch reaction process and continuous reaction process, in which, continuous reaction process using a fixed bed reactor is preferred ([0029]).
Regarding claim 10, US’233 teaches the obtained reaction mixture is subjected to simple distillation process to separate the intended α-olefin and other olefins including internal olefins ([0033]).
Regarding claims 1(c) and 21(c), US’233 fails to teach reacting the at least one alkene of step b) to obtain a product comprising at least one alkanediol having 5 to 15 carbon atoms. The deficiency is however cured by CA’095.
Regarding claims 1(c), 11 and 21(c), CA’095 teaches a process for producing vicinal diols by the reaction of olefinically unsaturated compounds containing 4 to 36 carbon atoms with hydrogen peroxide and formic acid followed by hydrolysis with a solution of caustic soda. The reference further teaches that the process may be applied with approximately equal results to linear olefins having terminal (also known as α-olefins) or internal double bonds and to cyclic olefins (pg.1,ln.31-pg.2,ln.1).
It is known to a skilled artisan that vicinal diols have various applications in the chemical industry, and thus a skilled artisan would have been motivated in subjecting the α-olefins and the internal olefin isomers of US’233 to the reaction methods of CA’095 with a reasonable expectation of success in obtaining vicinal alkanediols.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to a process for the preparation of alkanediols having 5 to 15 carbon atoms comprising the following steps: a) providing a 1-alcohol having 5 to 15 carbon atoms and/or a dialkylether having 10 to 30 carbon atoms and a catalyst; b) dehydrating the 1-alcohol and/or cleaving the dialkylether in a reaction chamber to obtain at least one alkene having 5 to 15 carbon atoms, wherein the at least one alkene having 5 to 15 carbon atoms is at least one olefin selected from the group consisting of: α-, β- and/or y-olefins; wherein the dehydration and/or cleavage is performed with recirculation of dialkylether and/or 1-alcohol; wherein the dialkylether and/or 1-alcohol are recirculated and combined with fresh 1-alcohol and/or fresh dialkylether, in a ratio of 30:70 to 50:50 by volume; and wherein the dehydration and/or cleavage is performed at a temperature ranging from 255 °C to 290 °C; and c) reacting the at least one alkene of step b) to obtain a product comprising at least one alkanediol having 5 to 15 carbon atoms in view of the combination of US’233 and CA’095.
Response to Arguments
The Applicant discusses the unexpected result of using recirculated dialkylether and/or 1-alcohol combined with fresh dialkylether and/or fresh 1-alcohol at a ratio of 30:70 to 50:50. Specifically, the Applicant discusses that the unexpected results are demonstrated by Examples 5 and 7 and further notes:
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Furthermore, the Applicant indicates that the above is highlighted in Table 6, the last three columns, that achieve excellent conversion and purity when compared to the first column where only fresh material is used. Applicant also notes that the selectivity and yield of the olefin do not decrease significantly.
The Applicant also argues
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The arguments are not persuasive. Firstly, the Applicant is arguing nonobviousness of the claimed invention based on unexpected results demonstrated in Examples 5 and 7 that encompasses a narrower specie of 1-alcohol and dialkylether, i.e. 1-heptanol and diheptyl ether, when the scope of the claimed invention encompasses a broader starting material comprising 1-alcohol having 5 to 15 carbon atoms and/or dialkylether having 10 to 30 carbon atoms. Thus, nonobviousness on the instant claims cannot be concluded based on the narrower data shown in Examples 5 and 7.
Furthermore, the Applicant has not clarified and explained how what is discussed in [256], specifically with respect to the statement “the recirculation of unreacted 1-alcohol and/or dialkyl ether, leads to a point at which dialkyl ether is cleaved than formed”, is achieved based on the data provided in Table 6. The examiner cannot decipher the connection of the data of Table 6 with the statement “the recirculation of unreacted 1-alcohol and/or dialkyl ether, leads to a point at which dialkyl ether is cleaved than formed”. What data value of Table 6 led to that conclusion?
The examiner disagrees with the arguments that "diheptyl ether" row of Table 6, the amount of ether is decreased for the claimed range of 30 : 70 to 50 : 50 recirculation ratios, since there is only between 22.2 to 25.9 wt.-% ether left in the product mixture, while about 30, 40 and 50 wt.-%. The 30, 40 and 50% set forth in Table 6 correspond volume % and not to wt% as Applicant argues. The specification discusses in para [252] how each of the volume% of Table 6 correspond to the weight percent of diheptyl ether (reproduced below) and shows that 30, 40 and 50 volume% does not directly correspond to 30, 40 and 50 wt% of diheptyl ether. Thus, the decrease in the amount of ether argued by the Applicant is not observed herein.
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Moreover, an increase in the conversion, selectivity and yield has not been achieved in the last three columns of Table 6 with recirculation when compared to the first column where only fresh starting material is used. In fact, the selectivity and yield decrease in the last three columns when compared to the first column. In terms of purity, only a slight increase in purity is achieved, i.e. from 96.3% (1st col) to 96.8% or 96.7% (last three columns) to the extent that such a small difference would not have made a great impact on the quality of the product. In fact, the instant specification describes in para. [298] as filed that a purity of 1-heptene at 91.1% is too low for industrial applications, whereas 96.4% purity is excellent. The purities obtained in Table 6 are even higher than the 96.4% that the specification notes as being excellent for industrial applications. As such, the purities achieved with recirculation are comparable to that obtained without recirculation.
Accordingly, one cannot conclude nonobviousness based on the data presented in Table 6 due to the lack of unexpected results.
The Applicant further discusses the unexpected and superior properties achieved by the large-scale production as shown in Example 7 in which a recirculation ratio of 40:60 has been used.
The examiner has considered the arguments, however, there is no comparative data in Example 7 where only a fresh starting material without recirculation has been used. Without such data, one would not be able to determine whether unexpected and superior properties have been achieved with recirculation.
The Applicant also notes that [259]-[260] discusses that the recirculation as instantly claimed allows milder reaction conditions such as temperatures below 280 °C. This is not persuasive because the reactions with and without recirculation are conducted at a milder temperature (Table 6). Hence, there is no criticality on the reaction conditions of recirculation over the process without the recirculation
In view of the foregoing, the instantly claimed invention remains obvious for reasons of record.
Claim 2 is rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US2003/0065233A1 (US’233) in view of Patent number CA1177095A (CA’095) as applied to claims 1, 3-11 and 21 above, and further in view of Patent number US11,4143,65 (US365). The references have been cited in PTO-892 12/23/2025.
The teachings of US’233 and CA’095 has been set forth above.
Regarding claim 2, CA’095 fails to specifically teach that the product comprises at least two alkanediols selected from the group consisting of: a 1,2-alkanediol, a 2,3-alkanediol and a 3,4-alkanediol, each independently having 5 to 15 carbon atoms; wherein in the product, the ratio of the 1,2-alkanediol to the 2,3-alkanediol is in the range of 90:10 to 99.9:0.1 and/or the ratio of the 1,2-alkanediol to the 3,4-alkanediol is in the range of 90:10 to 99.99:0.01 by weight.
However, since the reference teaches that the reaction process can be applicable to either the terminal olefins or internal olefins, subjecting any combination of the terminal olefins and internal olefins, such as 2,3-olefins or 3,4-olefins, would yield nothing more than the predictable product comprising at least two alkanediols selected from the group consisting of: a 1,2-alkanediol, a 2,3-alkanediol and a 3,4-alkanediol.
CA’095 teaches the desired diols can usually be obtained in reaction times of less than seven hours and in yields of approximately 90%.
Furthermore, US’365 teaches a composition comprising about 60% to about 99% of a bio-1,2-alkanediol having a carbon chain length of 7 to 20 carbon atoms and less than 20% of a corresponding bio-2,3-alkanediol having the same carbon chain length as the bio-1,2-alkanediol, which is equivalent to a ratio of bio-1,2-alkanediol to bio-2,3-alkanediol of 3:1 to 4.95:1. The reference teaches that the composition is used as a preservative composition.
Thus based on the general yield of diols taught by CA’095, it would be within the purview of a skilled artisan to determine, through routine experimentation, the amount needed for terminal olefins and 2,3-olefins to give a product composition of US’365 that comprises about 60% to about 99% of a bio-1,2-alkanediol having a carbon chain length of 7 to 20 carbon atoms and less than 20% of a corresponding bio-2,3-alkanediol having the same carbon chain length as the bio-1,2-alkanediol.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to a process for the preparation of alkanediols having 5 to 15 carbon atoms comprising the following steps: a) providing a 1-alcohol having 5 to 15 carbon atoms and/or a dialkylether having 10 to 30 carbon atoms and a catalyst; b) dehydrating the 1-alcohol and/or cleaving the dialkylether in a reaction chamber to obtain at least one alkene having 5 to 15 carbon atoms, wherein the at least one alkene having 5 to 15 carbon atoms is at least one olefin selected from the group consisting of: α-, β- and/or y-olefins; wherein the dehydration and/or cleavage is performed with recirculation of dialkylether and/or 1-alcohol; wherein the dialkylether and/or 1-alcohol are recirculated and combined with fresh 1-alcohol and/or fresh dialkylether, in a ratio of 30:70 to 50:50 by volume; and wherein the dehydration and/or cleavage is performed at a temperature ranging from 255 °C to 290 °C; and c) reacting the at least one alkene of step b) to obtain a product comprising at least one alkanediol having 5 to 15 carbon atoms; wherein in the product, the ratio of the 1,2-alkanediol to the 2,3-alkanediol is in the range of 90:10 to 99.9:0.1 and/or the ratio of the 1,2-alkanediol to the 3,4-alkanediol is in the range of 90:10 to 99.99:0.01 by weight in view of the combination of US’233, CA’095 and US’365.
Claim 22 is rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US2003/0065233A1 (US’233) in view of Patent number CA1177095A (CA’095) as applied to claims 1, 3-11 and 21 above, and further in view of Patent application publication number US2016/0206571A1 (US’571). The references have been cited in PTO-892 12/23/2025.
The teachings of US’233 and CA’095 has been set forth above.
Regarding claim 22, CA’095 does not specifically teach that the product obtained comprises at least two 1,2-alkanediols differing in their chain length. However, the reference teaches the process is particularly suitable for the hydroxylation of long-chain linear olefins containing 4 to 36 carbon atoms and a terminal or internal double bond.
Furthermore, US’571 teaches a composition comprising 1,2-alkanediols differing in their chain length, i.e. a mixture of 1,2-hexanediol and 1,2-octanediol, wherein the composition is used as active mixture in cosmetic, pharmaceutical or dermatological emulsions.
Thus, a skilled artisan would have been motivated to combine two terminal alkenes with 6 and 8 carbon numbers and subject the mixture to the reaction process of CA’095 with a reasonable expectation of success in obtaining a combination of 1,2-hexanediol and 1,2-octanediol that can be used as active mixture in cosmetic, pharmaceutical or dermatological emulsions.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to a process for the preparation of alkanediols having 5 to 15 carbon atoms comprising the following steps: a) providing a 1-alcohol having 5 to 15 carbon atoms and/or a dialkylether having 10 to 30 carbon atoms and a catalyst; b) dehydrating the 1-alcohol and/or cleaving the dialkylether in a reaction chamber to obtain at least one alkene having 5 to 15 carbon atoms, wherein the at least one alkene having 5 to 15 carbon atoms is at least one olefin selected from the group consisting of: α-, β- and/or y-olefins; wherein the dehydration and/or cleavage is performed with recirculation of dialkylether and/or 1-alcohol; wherein the dialkylether and/or 1-alcohol are recirculated and combined with fresh 1-alcohol and/or fresh dialkylether, in a ratio of 30:70 to 50:50 by volume; and wherein the dehydration and/or cleavage is performed at a temperature ranging from 255 °C to 290 °C; and c) reacting the at least one alkene of step b) to obtain a product comprising at least one alkanediol having 5 to 15 carbon atoms; and wherein in step c) the product obtained comprises at least two 1,2-alkanediols differing in their chain length and/or wherein the product comprises at least two 2,3-alkanediols differing in their chain length, and wherein said alkanediols each independently have from 5 to 15 carbon atoms in view of the combination of US’233, CA’095 and US’571.
Response to Arguments
The Applicant argues that US’365 and US’571 fails to teach the use of mixtures of fresh and recycled alcohol and ether. Specifically, the Applicant argues that US’365 teaches away from said mixture by stating “no recycle stream used whatsoever” and that US’571 is drawn with the use of 1,2-alkanediols in active mixtures with no teachings how to prepare the compounds. Thus, the Applicant argues that the references fail to cure the deficiencies of US’233.
The examiner disagrees. As made of record and discussed above, the use of mixtures of fresh and recycled alcohol and ether is obvious in view of the teachings of US’233. US’365 and US’571 are presented as references that teach the motivation in obtaining the product composition of claims 2 and 22. Thus the 103 rejection of claims 2 and 22 are maintained for reasons discussed above.
Citation of Relevant Prior Art
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Patent number GB2145076A (GB’076; cited in PTO-892 12/23/2025) teaches
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Thus, the process of the instant claims 1 and 21 would be obvious over the combination of US’233 (cited above) and GB’076.
Note: This is not a 103 rejection, but making the additional reference, GB’076, of record as a relevant art and how it would make the instant claim obvious when combined with the teachings of US’233.
Conclusion
Claims 1-7, 9-11 and 21-22 are rejected and no claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
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/MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692
